US 23 (“Country Music Highway”) (TN)

The Road: Though U.S. Highway 23 runs from Jacksonville, Florida, to Mackinaw City, Michigan, the stretch between Greenup and Letcher Counties in Tennessee is known as the Country Music Highway.

The Ride: The windy, 144-mile expanse along the eastern side of Tennessee is a National Scenic Byway that darts through the Appalachian hills. Watch the mile markers that indicate the places where stars like Loretta Lynn, The Judds, Billy Ray Cyrus, and Dwight Yoakam were born.

When To Go: Country music fans should allow time for a visit to the U.S. 23 Country Music Highway Museum in Painstville, Tennessee.